Edward Wilson (Matt Damon) is the coldest fish in the cold war. A quiet guy, he only speaks when he absolutely has something to say. When he's not speaking, he's watching, listening, and formulating a plan of attack. From what anyone can tell, his is a stoicism culled from a sense of honor and patriotism. He finds betrayal and personal slights particularly offensive, and his father's last words before committing suicide have made Edward wary of people who are living a lie. He naturally suspects that no one may be who they seem, and thus, he'll make the perfect spy.

The Good Shepherd has been a pet project of Robert De Niro's for a decade now, almost since his last directorial effort, A Bronx Tale. It seems natural that an actor would want to make a movie about the beginnings of the CIA. In the counterintelligence business, everyone is playing a part, trying on new identities, and speaking in carefully scripted dialogue. So much so, they tend to lose focus of everything around them. It's all about the job.

This fictionalized account of the creation of America's international spy program runs on two alternating timelines. It opens in 1961, as Edward Wilson spearheads the failed Bay of Pigs offensive. Convinced that someone from within his organization tipped off the Russians--"There's a stranger in our house," he tells his assistant, Ray Brocco (John Turturro, Secret Window)--he needs to expose the leak or risk getting plugged up himself. The answer may lie in a mysterious audio tape and photograph of a lovers' rendezvous that was shoved under his door--or it may not. Nothing is as it seems, and what looks like a lead could just be further misinformation.
That's actually one of the first lessons Wilson learns in the other story line, the one that starts at Yale in the 1930s and follows the character into the OSS and WWII. He's told by his mentor (Michael Gambon, Layer Cake) that the true power in counterintelligence is making your enemy think he knows something when he really doesn't. Wilson is warned more than once that no one is his friend and there is not a single person on earth he can trust. This extends even into his personal life, and he alienates his wife (Angelina Jolie) and child.

I think it's a prerequisite of CIA stories that they have to be long and extremely complicated. Norman Mailer's novel on the subject, Harlot's Ghost, for instance, is 1300 pages long. The Good Shepherd is over two and a half hours. It's slow, methodical, and you don't always know on which side the coin ultimately lands, but at the same time, it's hard not to be sucked into its vortex of information and I was surprised to look at my watch and see as much time had passed as did. The idea seems to be to put the viewer in Wilson's shoes, catching us in the riptide of international politics and the self-replicating nature of covert organizations. Wilson starts by joining the Skull and Bones Society at Yale, then helping the FBI (in the form of Alec Baldwin) pull off an undercover sting, and on to the OSS and CIA. Other agents move in and out of the plot, and just as soon as one foe is toppled, the victor must instantly create another in order to keep going. Hitler gives over to the outgrowth of the USSR, and then to Castro, and by that point, it's all so twisted, the spies are feeding on themselves. Double agents, triple agents, imposters--it's all par for the course.

Some of the movie could have probably been trimmed down. There are multiple red herrings that may or may not be significant. A dollar bill pops up early in the movie, and then maybe returns later on, but it's not really clear why. Wilson enters into a pact with a mobster (Joe Pesci), but beyond the initial meeting, nothing really comes from it. Are such plot points dangling there to confuse us on purpose or by accident?

Matt Damon puts in an interesting performance as Wilson. For an actor, a role where you reveal more about yourself by revealing nothing must be quite a challenge. The way he walks through the movie with a stony expression at times makes it hard not to think of his savagely empty-headed portrayal by a puppet in Team America. Yet, he somehow manages to give Wilson a soul to lose. He makes good use of the scenes from the past that break the character's heart, such as his father's suicide and the first time he had to lead a colleague down the garden path to his own demise. Most effective is his first romance, with the deaf co-ed Laura (Tammy Blanchard, Life with Judy Garland). For a man who doesn't like to speak, a woman who doesn't rely on sound is his perfect soulmate. When he ultimately has to let go of his affection toward her, it's the final betrayal he can inflict upon himself. After that, there is no going back.

In the end, opinions will probably split on The Good Shepherd. De Niro has made a risky movie that deglamorizes espionage and shows it for what it really is, an often tedious and plodding game where information is deadlier than bullets. If you can get into watching the ball unravel, the film will likely hold your interest until you get to its center, but you have to be prepared to go all in and maybe get a little caffeinated beforehand. Spying is a business not everyone is cut out for, after all.